Exam 2 Key 2009

Exam 2 Key 2009 - Chauhan Hanish 8[0204535 CHEMISTRY 2211...

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Unformatted text preview: Chauhan, Hanish 8 [0204535 lllllllllfllllllllllllllllll Illlllllllllmlllllllll CHEMISTRY 2211 EXAM 2 March 4, 2009 S RE Be sure to read each question carefully. Partial credit will be assigned where appropriate. 1 To receive full credit you must answer the question completely. Relax and good Iuc .. . l (10 pts) Provide the proper IUPAC names for the following compounds in the spaces provided below: ‘I )9 WWW} 2. (10 points) Looking down the Carbon 2 — Carbon 3 bond of 3-chloro-Z-methylpentane, provide the following: Draw all three staggered conformations, circle the most stable conformer and calculate its total strain energy: ‘ as _ a l Draw all three eclipsed conformations, circle the least stable conformer and calculate . . L \ ltS total strain energy: ‘ ’gilt (is Energy H014 364 elm-4M 3. (] 0 pts) Draw a reaction energy diagram that corresponds to the following criteria: i. The first step is the slowest of the three and has a positive AH“ ii. The second step is fast and exothermic iii. The third step is slow and has a positive AG“ iv. The reaction’s overall Keq< 1 (CV Clearlv label each individual step’s activation energv and transition state as well as the AG” of the overall reaction. Make sure that your labeling is neat and clear: Reaction Progress 4. (10 pts) Draw the two possible chair conformations of the following compound. Your structures must adhere to the indicated numberin scheme. Calculate the total strain energy of each conformation and circle the most stable conformer. Ring Flip -\. Draw the most stable chair con ormation of cis-l-tert-butyl-4-ethylcyclohexane in the box—)’ provided below: 717 r : HM! 5% AW 5. (6 pts) Assign the appropriate E/Z stereochemistry to the alkenes provided below: It 1 0 m 6%? 4o 6% G O 0\ (B E a (6 pts) Calculate the degrees of unsaturation in the following molecular formulas: Zh/LL‘ UL 19stBr2FN02 S 3< zucovwo—azs 12s- C63???) : o A? Z, lelsBrCle ; Z 6. 15) +2) ‘33 Zn 7. (10 pts) Add curved arrows to the mechanism provided below to indicate the appropriate electron movement in each step: H I NH2 + Q @Nfl. NH4 \H + NH3 8. (ii) pts) Draw the complete reaction mechanism for the following radical reaction: h Cl V \/\ + Cl: ———"“ \/l\ + HCI Monochlorination of n—butane Provide the appropriate reactants, intermediates, and products in the boxes below. You must also provide the appropriate arrows to clearly account for all electron movement. Initiation: /“/M//( 9. (8 pts) Igotify the following reactions as ad Ition, elimination, subsflétion, or rearran ment in the box provided to righ of each equation: 10. (8 pts) Indicate whether the following pairs of compounds are constitutional isomers, stereoisomers, conformational isomers, or identical to one another: CH3 CH3 M l; UHQSYH / egg,“ 1]. (10 pt) Calculate the heat of formation (AHO) for the following reaction using the appropriate bond dissociation energies found in the tables provided with your test. In order to receive full credit, vou must show all of vour work: CchHzBr + H20 —"——>" CH3CH20H Hydration of Bromoethane AHO = “‘7 Is this reaction endothermic or exothermic? Calculate the AG for this reaction ifthe change in entropy is 138° = 0.045 KJ/mol at a temperature of 323K. Show vour work: akin 53 $953!? 3°"d,,‘?3§§9‘.iifi.‘591‘.51299???» § B 0 Bend (Rd/mo!) Bond {kJImoIi Bond {lemnD H-“H 436 1_CH3}gC-l 209 CZHs—CHa 355 Pia-F 570 H2C=CH—H 444 (CH332CH—CH3 351 Fin-Cl 432 HQCECH—CI 368 (CH3)3C—CH3 339 HmBr _ 366 H2C=CHCH2~H 36} H2C=CHwCH3 406 E‘- 8—! 298 Hat-TCHCHQWG 289 Hacchcsafi—m3 310 ca—m 243 H H2C=CH2 61] Btu-Jar 193 0/ 464 CH3 3m; , 151 Q/ 427 CBS—H 438 CI CHy—Ci 351 0/ 405 CszCfis mama: 293 O 332 (3143—! 23-4 (:sz H CH3“ OH 380 368 H 368 6143— NH; 335 CH3C:H 3 2007 Thomson Higher Education H mH 420 _c1 02 s CH2 HOWH 8 Cszw—Ci 338 293 , HID-"OH 21 3 C-ZHs—Br 285 M CH30~H 43? C2H5—i .222 Cfigs—H 371 C2H5WGH 380 33 7 fl— £2H50~H 436 O (CH } (EH-“CE 339 ,0}; 5| 3 2 / (mac “CH3 3’22 (CH312CHMBr 274 3 469 . \ (Ci-1313C“?! 39D CH3CH20—CH3 339 ICHaigc-"Cl 330 “CEO—H 552 NHZ—H 449 (CH3)3C~— Br 263 CHawCHa 3 76 H—CN 518 3 2007 Thomson Highs! Educanon / Table 4.1 Energy Costs for Interactions in Alkane Conformers H H Eclipsed H -- CH3 Eclipsed H —- CHZCH3 Eclipsed H —— Br Eclipsed CH3 -- CH3 Eclipsed CH3 -- CHzCHs Eclipsed CH2CH3 -- CH20H3 Eclipsed ON ON Eclipsed CH3 —— Br Eclipse-d CI -— CI Gauche CN r- CN Gauche CI -- CN Gauche CH3 -- CN Gauche CH3 -- CH3 Gauche CH3 -— CHZCHa Gauche _C;H3 §-_C| aughefiifi_ CH2CH3 -- CI Gauche ' ' 7 Table 4.2 Steric Strain in Monosubstituted Cycloalkanes >¢Fm~zEIUmeth : 5.1: LC.» 2925.. LLCLfifizfi .meEEmEUxucEcm Eur—«3: .5» SEE. Lbcmrdpm 2 m: .8 E mm me E mm mm mm .. =m ..Ew Em =2 .5 .3 9. ,5? N. 3%, T E: 7 :3: n. 22: m. NE: : .1 965m Ucm NH mEmeE .2 End: IVE E 8533 9: $850.. .055. .3 mmEm: ESE *0 Banana 9: :E: Em: ma ___3 m9. m>onm EunEzc EEEm E mEmESm 22 202E? ucm mem: ucmEEmi 9F. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .- 3.3.2.9. 3.2.“.37 N: EL. mu: 2:. he. a m3. me. 2.: an mm 25 25 ES :2 m: :m m an E 2 mm :5 5,: ES... :2: Eu: Ex. 5.: 52.. E: t :52 n. m: E.“ 3.2.8.2. B $3.33. 272.3. wéamé, 43.2.2. 223:. 372.5. #53:. Eimé. $72.2. 332.. 373.2. 7:75.?N mm mm 3 mm 5 an E. m... .2. E. E. :m E on 5 :. a: .2 E : 3 .am 3 .3 m. I n. n. a. _: .1. m. .52 “4 5:: n4 curd—um nmn En .4 mmdtm T 302%: m. EH5: a. mu 9.: 7 n5: “1 , 79.2.3 79.5.3 mu 3. =m .. 9 EH»: do m.3.m.w NAT?“ 7mg.” mm en .2 mm mu— WW:_>_ MLQ w> M“ 25¢ N. 52% m+ .39.; N» $55.. 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Exam 2 Key 2009 - Chauhan Hanish 8[0204535 CHEMISTRY 2211...

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